(3β,5β)-3-<(3',4',6'-tris-O-(p-nitrobenzoyl)-2'-deoxy-β-D-arabino-hexopyranosyl)oxy>-14-hydroxycard-20(22)-enolide | 88253-69-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (3β,5β)-3-<(3',4',6'-tris-O-(p-nitrobenzoyl)-2'-deoxy-β-D-arabino-hexopyranosyl)oxy>-14-hydroxycard-20(22)-enolide
• CAS: 88253-69-4
• 化学式: C₅₀H₅₃N₃O₁₇
• 分子量: 967.981
• InChiKey: SUFDRRUJRRXENG-UVASKEMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.78
• 重原子数：
  70.0
• 可旋转键数：
  13.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  273.31
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  (3β,5β)-3-<(3',4',6'-tris-O-(p-nitrobenzoyl)-2'-deoxy-β-D-arabino-hexopyranosyl)oxy>-14-hydroxycard-20(22)-enolide 在 potassium hydrogencarbonate 作用下， 以 甲醇 为溶剂， 反应 288.0h， 以56.3%的产率得到(3β,5β)-3-<(2'-deoxy-β-D-arabino-hexopyranosyl)oxy>-14-hydroxycard-20(22)-enolide
  参考文献：
  名称：

  Cardiac glycosides. 1. A systematic study of digitoxigenin D-glycosides

  摘要：

  A series of digitoxigenin glycosides was studied: five with beta-D-sugars varying stepwise in sugar structure from beta-D-digitoxose to beta-D-galactose, including one beta-D/alpha-D pair. I50 values for these glycosides and digitoxigenin were determined with hog kidney Na+, K+-ATPase. These data suggest a major and unexpected role for 4'-OH conformation in the sugar. All the glycosides with an equatorial 4'-OH were more active than the two with the 4'-OH axial [digitoxigenin beta-D-galactoside (6) I50 = 6.45 X 10(-8) M; digitoxigenin 2'-deoxy-alpha-D-ribo-hexopyranoside (alpha-3a) I50 = 9.33 X 10(-8) M; digitoxigenin I50 = 1.17 X 10(-7) M]. Stereochemistry of the 3'-OH had much less of an activity role than that of the 4'-OH, in contrast to existing models of "sugar-site" binding.

  DOI：

  10.1021/jm00369a004
• 作为产物：
  描述：

  2-Desoxy-3,4,6-tri-O-(4-nitro-benzoyl)-D-arabino-hexosylchlorid 、 毛地黄毒苷配基 在 silver carbonate 作用下， 以 四氯化碳 、 1,2-二氯乙烷 为溶剂， 反应 2.5h， 以59.8%的产率得到(3β,5β)-3-<(3',4',6'-tris-O-(p-nitrobenzoyl)-2'-deoxy-β-D-arabino-hexopyranosyl)oxy>-14-hydroxycard-20(22)-enolide
  参考文献：
  名称：

  Cardiac glycosides. 1. A systematic study of digitoxigenin D-glycosides

  摘要：

  A series of digitoxigenin glycosides was studied: five with beta-D-sugars varying stepwise in sugar structure from beta-D-digitoxose to beta-D-galactose, including one beta-D/alpha-D pair. I50 values for these glycosides and digitoxigenin were determined with hog kidney Na+, K+-ATPase. These data suggest a major and unexpected role for 4'-OH conformation in the sugar. All the glycosides with an equatorial 4'-OH were more active than the two with the 4'-OH axial [digitoxigenin beta-D-galactoside (6) I50 = 6.45 X 10(-8) M; digitoxigenin 2'-deoxy-alpha-D-ribo-hexopyranoside (alpha-3a) I50 = 9.33 X 10(-8) M; digitoxigenin I50 = 1.17 X 10(-7) M]. Stereochemistry of the 3'-OH had much less of an activity role than that of the 4'-OH, in contrast to existing models of "sugar-site" binding.

  DOI：

  10.1021/jm00369a004